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Developing Structural First Principles for Alkylated Triphenylphosphonium-Based Ionic Liquids.

ABSTRACT: While ionic liquids have proved to be versatile materials for a wide spectrum of applications, e.g., energy, materials, and medicine, several challenges remain concerning the rational design of novel materials. In light of this, a series of four triphenylphosphonium-based ionic liquids have been synthesized for the first time. These compounds exhibit high thermal stability with decomposition temperatures up to 450 °C. Their solid-state structures are characterized by single-crystal X-ray diffraction and the intermolecular interactions rigorously analyzed via Hirshfeld surface analysis. It was found that the unique geometries of the anions used in the study form distinct interactions with the cations. The interactions in the crystalline state are correlated with the thermal properties of the four ionic liquids to rationalize the melting points and phase transitions for each compound. The observed arrangements of the alkyl chains on the cations are investigated computationally to gain an understanding of how rotational freedom may impact the thermal properties of the compounds. By intention, each IL reported in this work offers a unique property profile and contributes to the ever-growing ionic liquid catalog.

SUBMITTER: O'Rourke B

PROVIDER: S-EPMC8638304 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Transcriptional toxicity of imidazolium- and cholinium-based ionic liquids

Project description:Ionic Liquids are a broad group of salts with low melting points that can be specifically tuned for a broad range of applications. Despite being initially considered “green” solvents, their better environmental friendliness compared to traditional solvents has been increasingly challenged. In this study, we aimed to investigate the molecular effects of ILs exposure by using RNA-sequencing to study differential gene expression patterns. Thus, we exposed Daphnia magna to 1-ethyl-3-methylimidazolium chloride ([C2mim]Cl), 1-dodecyl chloride-3-methylimidazolium ([C12mim]Cl) and cholinium chloride ([Chol]Cl). Results suggest that the three ILs share several mechanisms of toxicity, including cellular membrane and cytoskeleton damage, oxidative stress, inhibition of antioxidant enzymes, mitochondrial affectation, changes in protein biosynthesis and energy production, DNA damage, and ultimately, programmed cell death and disease initiation. Overall, the dataset revealed that [C2mim]Cl and [C12mim]Cl were, respectively, the least and the most toxic ILs at the transcriptional level. Also, it is reinforced that [Chol]Cl is not devoid of environmental hazardous potential. Unique gene expression signatures could also be identified for each IL.

2021-08-13 | GSE156769 | GEO

Transcriptional toxicity of imidazolium- and cholinium-based ionic liquids

Project description:Transcriptional toxicity of imidazolium- and cholinium-based ionic liquids

| PRJNA659001 | ENA

Physicochemical and structural properties of lidocaine-based ionic liquids with anti-inflammatory anions.

Project description:The purpose of this paper was to examine the density, viscosity and electrical conductivity at different temperatures, as well as the thermal stability and structural properties of previously reported ionic liquids based on active pharmaceutical ingredients. Lidocaine-based ionic liquids, with ibuprofen and salicylate as counterion, were prepared first. Their structures were confirmed by infrared, mass and 1H and 13C nuclear magnetic resonance spectroscopy. The Newtonian behaviour of lidocaine ibuprofenate was confirmed from viscosity measurement results, while it was impossible to determine for lidocaine salicylate. The interactions and structures of the studied ionic liquids were analyzed based on the measured density values, viscosity, electrical conductivity, and calculated values of thermal expansion coefficients and activation energy of viscous flow. From a theoretical aspect, DFT and MD calculations were performed. The obtained descriptors and radial distribution, as well as structural functions, were used to understand the structural organization of the synthesized ionic liquids.

| S-EPMC9051649 | biostudies-literature

Enhancing the Catalytic Performance of Candida antarctica Lipase B by Chemical Modification With Alkylated Betaine Ionic Liquids.

Project description:Various betaine ionic liquids composed of different chain lengths and different anions were designed and synthesized to modify Candida antarctica lipase B (CALB). The results showed that the catalytic activity of all modified lipases improved under different temperature and pH conditions, while also exhibiting enhanced thermostability and tolerance to organic solvents. With an increase in ionic liquid chain length, the modification effect was greater. Overall, CALB modified by [BetaineC16][H2PO4] performed best, with the modified CALB enzyme activity increased 3-fold, thermal stability increased 1.5-fold when stored at 70°C for 30 min, with tolerance increased 2.9-fold in 50% DMSO and 2.3-fold in 30% mercaptoethanol. Fluorescence and circular dichroism (CD) spectroscopic analysis showed that the introduction of an ionic liquid caused changes in the microenvironment surrounding some fluorescent groups and the secondary structure of the CALB enzyme protein. In order to establish the enzyme activity and stability change mechanisms of the modified CALB, the structures of CALB modified with [BetaineC4][Cl] and [BetaineC16][Cl] were constructed, while the reaction mechanisms were studied by molecular dynamics simulations. Results showed that the root mean square deviation (RMSD) and total energy of modified CALB were less than those of native CALB, indicating that modified CALB has a more stable structure. Root mean square fluctuation (RMSF) calculations showed that the rigidity of modified CALB was enhanced. Solvent accessibility area (SASA) calculations exhibited that both the hydrophilicity and hydrophobicity of the modified enzyme-proteins were improved. The increase in radial distribution function (RDF) of water molecules confirmed that the number of water molecules around the active sites also increased. Therefore, modified CALB has enhanced structural stability and higher hydrolytic activity.

| S-EPMC8899502 | biostudies-literature

Novel Ionic Conducting Composite Membrane Based on Polymerizable Ionic Liquids.

Project description:In this work, the design and characterization of new supported ionic liquid membranes, as medium-temperature polymer electrolyte membranes for fuel-cell application, are described. These membranes were elaborated by the impregnation of porous polyimide Matrimid® with different synthesized protic ionic liquids containing polymerizable vinyl, allyl, or methacrylate groups. The ionic liquid polymerization was optimized in terms of the nature of the used (photo)initiator, its quantity, and reaction duration. The mechanical and thermal properties, as well as the proton conductivities of the supported ionic liquid membranes were analyzed in dynamic and static modes, as a function of the chemical structure of the protic ionic liquid. The obtained membranes were found to be flexible with Young's modulus and elongation at break values were equal to 1371 MPa and 271%, respectively. Besides, these membranes exhibited high thermal stability with initial decomposition temperatures > 300 °C. In addition, the resulting supported membranes possessed good proton conductivity over a wide temperature range (from 30 to 150 °C). For example, the three-component Matrimid®/vinylimidazolium/polyvinylimidazolium trifluoromethane sulfonate membrane showed the highest proton conductivity-~5 × 10-2 mS/cm and ~0.1 mS/cm at 100 °C and 150 °C, respectively. This result makes the obtained membranes attractive for medium-temperature fuel-cell application.

| S-EPMC8588533 | biostudies-literature

Structural, mechanical and electronic properties and hardness of ionic vanadium dihydrides under pressure from first-principles computations.

Project description:Based on a combination of the CALYPSO method for crystal structure prediction and first-principles calculations, we explore the crystal structures of VH2 under the pressure range of 0-300?GPa. The cubic Fm-3m phase with regular VH8 cubes is predicted to transform into orthorhombic Pnma structure with fascinating distorted VH9 tetrakaidecahedrons at 47.36?GPa. Both the Fm-3m phase at 0?GPa and the Pnma phase at 100?GPa are mechanically and dynamically stable, as verified with the calculations of elastic constants and phonon dispersions, respectively. Moreover, the calculated electronic band structure and density of states indicate both stable phases are metallic. Remarkably, the analyses of the Poisson's ratio, electron localization function (ELF) and Bader charge substantiate that both stable phases are ionic crystals on account of effective charges transferring from V atom to H. On the basis of the microscopic hardness model, the Fm-3m and Pnma crystals of VH2 are potentially incompressible and hard materials with the hardness values of 17.83 and 17.68?GPa, respectively.

| S-EPMC7264295 | biostudies-literature

A comparative study of ammonia solubility in imidazolium-based ionic liquids with different structural compositions.

Project description:Four imidazolium-based ionic liquids (ILs) with two cations 1-pentyl-3-butylimidazolium [PBIM]+ and 1-benzyl-3-butylimidazolium tetrafluoroborate [BzBIM]+, and two anions tetrafluoroborate (BF4-) and trifluoromethanesulfonate (OTf-) were synthesized for NH3 solubility enhancement. The structural, thermal, and electrochemical stabilities, ionic conductivity, and viscosity of the four ILs, namely, [PBIM]BF4, [BzBIM]BF4, [PBIM]OTf, and [BzBIM]OTf, were investigated. Due to the intermolecular interaction of the benzyl group attached to the imidazolium ring, [BzBIM]+-based ILs exhibited higher thermal stability but lower ionic conductivity compared to [PBIM]+-based ILs. Further, the NH3 solubility in all ILs was measured using a custom-made setup at temperatures ranging from 293.15 to 323.15 K and pressures ranging from 1 to 5 bar. The effects of the cation and anion structures of ILs, as well as pressure and temperature, on the NH3 solubility in the ILs were also investigated. [PBIM]BF4 showed the best solubility because of its high free volume and low viscosity. Density functional calculations validated the superior NH3 solubility in [PBIM]BF4, attributable to the minimal reorganization of the [cation]anion complex geometry during the solvation process, yielding a low solvation free energy. The findings of this study suggest that ILs exhibit a high NH3 solubility capacity and cation and anion structures considerably affect the NH3 solubility in ILs.

| S-EPMC10826666 | biostudies-literature

Tetrahydrothiophene-Based Ionic Liquids: Synthesis and Thermodynamic Characterizations.

Project description:S-alkyltetrahydrothiophenium, [Cn THT]+ bis(trifluorosulfonyl)imide, [NTf2 ]- room temperature ionic liquids (ILs) and tetraphenylborate, [BPh4 ]- salts with alkyl chain lengths from C4 to C10 have been prepared. The ILs and salts were characterized and their purity verified by 1 H- and 13 C-nuclear magnetic resonance, elemental analysis, ion chromatography, Karl-Fischer titration, single crystal X-ray diffraction as well as thermogravimetric analysis. The experimentally determined density and viscosity decrease with increasing temperature. The experimental solubility of the [Cn THT][NTf2 ]-ILs in water (75 to 2.2 mg/L for C4 to C10 ) was modelled with very good agreement by Perturbed Chain Statistical Associating Fluid Theory (PC-SAFT), based on the extremely low vapor pressures for the [Cn THT][NTf2 ]-ILs measured in this work (4.15 to 0.037 ⋅ 10-7 ×psat for C4 to C10 ). PC-SAFT is able to predict and correlate different thermodynamic properties by estimating the Helmholtz residual energy.

| S-EPMC7874261 | biostudies-literature

Structural Reorganization of Imidazolium Ionic Liquids Induced by Pressure-Enhanced Ionic Liquid-Polyethylene Oxide Interactions.

Project description:Mixtures of polyethylene oxide (PEO, M.W.~900,000) and imidazolium ionic liquids (ILs) are studied using high-pressure Fourier-transform infrared spectroscopy. At ambient pressure, the spectral features in the C-H stretching region reveal that PEO can disturb the local structures of the imidazolium rings of [BMIM]+ and [HMIM]+. The pressure-induced phase transition of pure 1-butyl-3-methylimidazolium bromide ([BMIM]Br) is observed at a pressure of 0.4 GPa. Pressure-enhanced [BMIM]Br-PEO interactions may assist PEO in dividing [BMIM]Br clusters to hinder the aggregation of [BMIM]Br under high pressures. The C-H absorptions of pure 1-hexyl-3-methylimidazolium bromide [HMIM]Br do not show band narrowing under high pressures, as observed for pure [BMIM]Br. The band narrowing of C-H peaks is observed at 1.5 GPa for the [HMIM]Br-PEO mixture containing 80 wt% of [HMIM]Br. The presence of PEO may reorganize [HMIM]Br clusters into a semi-crystalline network under high pressures. The differences in aggregation states for ambient-pressure phase and high-pressure phase may suggest the potential of [HMIM]Br-PEO (M.W.~900,000) for serving as optical or electronic switches.

| S-EPMC7835789 | biostudies-literature

The effect of structural heterogeneity upon the microviscosity of ionic liquids.

Project description:The behaviour of two molecular rotors, one charged - 3,3'-diethylthiacarbocyanine iodide (Cy3) and one neutral - 8-[4-decyloxyphenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY-C10), have been studied in various ionic liquids. The fluorescent decay lifetime has been used to elucidate the structure of the immediate region around the rotor. The neutral BODIPY-C10 was found to prefer the non-polar alkyl chain environment, leading to two trends in the lifetime of the dye: one when it was fully partitioned into the non-polar domain, and one when it also sampled polar moieties. The positively charged Cy3 dye showed a complex relationship between the bulk viscosity of the ionic liquid and lifetime of the molecular rotor. This was attributed to a combination of polarity related spectral changes, changes in anion cages around the dye, and temperature dependent fluorescent lifetimes alongside the dependence of the rotor upon the viscosity.

| S-EPMC7448533 | biostudies-literature

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